This article is about how African Americans in New York City in the 1820s, 1830s, and 1840s negotiated with whites that intensely human moment at the center of all monetary exchanges. The piece is based on decades of reading court cases and newspapers and in it I detail the mostly previously unknown experiences of a host of ordinary African Americans ranging from from petty entrepreneurs through to petty con men. This article, then, is part of my long-standing effort to recover the lives of African Americans living in New York City in the first half of the nineteenth century.